


Something New

by thewinchesterlifestyle



Category: Supernatural
Genre: Age Difference, Age Difference Kink, Anal Fisting, Anal Gaping, Bottom Castiel, Dirty Talk, Family Friend Benny, Fingering, Fist Fucking, Fisting, Implied Top Benny, Light Dom/sub, M/M, Orgasm Delay, Past Castiel/Other(s), Past Double Penetration, Past Threesome, Power Imbalance, Praise Kink, Secret Relationship, Size Difference, Size Kink, Teen Castiel, Training, because in this one Benny did take advantage of Cas's age and lack of knowledge, dubcon, older benny
Language: English
Status: Completed
Published: 2017-05-30
Updated: 2017-05-30
Packaged: 2018-11-07 00:51:48
Rating: Not Rated
Warnings: Underage
Chapters: 1
Words: 1,926
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11047872
Author URL: https://archiveofourown.org/users/thewinchesterlifestyle/pseuds/thewinchesterlifestyle
Summary: “Gorgeous.” Benny breathed in appreciation from somewhere behind him and Castiel couldn’t stop the flush from spreading across his cheeks.





	Something New

**Author's Note:**

> Written for a prompt.
> 
> Make sure to read the tags before continuing.

Castiel gripped the slats of the bed and shifted his legs into a more comfortable position that still offered his exposed hole to Benny. He could hear the older man moving around the room, humming under his breath, as he stripped and collected the large bottle of lube.

“ _Gorgeous_.” Benny breathed in appreciation from somewhere behind him and Castiel couldn’t stop the flush from spreading across his cheeks. Ever since he’d found himself in bed with his parents’ friend the older man always made sure to let him know how beautiful he was and how good. He should be with someone closer to his age, someone not _illegal_ , but Castiel loved how good Benny made him feel. “You’re gonna look even more gorgeous takin’ my fist, angel.”

The bed dipped and Castiel swallowed roughly. He had taken dildos of various sizes and two cocks at the same time when Benny had invited a friend over for a wild night that had left him sore in all the right ways.

But he’d never taken a fist.

He had never had Benny’s whole hand inside him, stretching him and filling him up. But Benny had always set the pace. He had done so since he’d told Castiel this was their secret and that he was going to make him feel good.

Castiel’s fingers gripped the bed tighter and his ass clenched down around nothing at the very thought. “Gettin’ excited?” a hand stroked over his ass affectionately while Benny’s thumb on his other hand rubbed against his rim. “I know I am.”

There was a soft  _click_  of the lube bottle opening and Castiel’s cock ached, forgotten and not to be touched, while Benny slicked his fingers up. The first finger was easy, he was still slightly loose and sloppy from the rough fucking earlier.

“Can’t wait to fuck you full of my fist. To see that tiny hole gaping.” Benny’s thick finger pumped into him a few times, pressing against his inner walls, as it loosened him up enough to comfortably start to take two fingers. They scissored inside him and twisted to where they lightly brushed his prostate. Castiel jolted, moaning lowly as pleasure burst through him. “You’re going to feel it tomorrow when you’re sittin’ in class.”

Without thought Castiel moaned and shoved his ass back into Benny’s motions. He wanted Benny’s fingers deeper, wanted to be spread open and full, but Castiel knew it wasn’t just going to be Benny’s fingers inside of him when this was done.

The fingers inside of him stilled and Castiel growled in annoyance. He didn’t want to be teased, he wanted Benny to move and he wanted the warm pleasure curling inside of him to build. “I’m in charge, angel. _No moving_.” Benny’s voice was firm but didn’t hold any annoyance or anger. It carried with it the tone of someone in charge, someone far older, and Castiel bowed to Benny’s control. Castiel closed his eyes and twisted his fingers around the wooden slats as he forced himself to relax. “ _Good boy_.”

A hand pet him gently in reward and Benny’s fingers resumed their earlier motions. They lazily fucked in and out of his hole, catching on his sensitive rim, as Castiel struggled not to push back into them to take them deeper. He just wanted to turn around and sink down onto Benny’s cock so he could ride him until he came.

He had never been good with patience, not since he’d learned how good it felt to be fucked, but Benny frequently tied him up and he had to be patient until Benny freed him. Benny’s promise, _Don’t worry, angel, I’ll make sure you train you how to please a man_ floated through his mind as his body trembled.

Benny’s three fingers started to stretch him and Castiel could feel the burn. They were slowly working to loosen him up and he struggled to imagine Benny’s  _whole fist_  inside him. There was no way he could take that kind of size. Benny’s fist was monstrous.

Two thick cocks had been impressive. Benny’s hand and wrist? That couldn’t possibly work. Benny hadn’t even used the biggest dildo on him yet but Castiel was going to be taking a fist.

When the fourth finger was added, along with more lube, Castiel could feel his thighs shaking and his muscles straining. He couldn’t help but clench down on instinct and a whimper escaped at the burn. “Such a greedy lil’ hole.” Benny’s voice was getting rougher and Castiel could hear more of Benny’s accent. “All wrapped ‘round my fingers. Takin’ ‘em so good. Such a sweet little angel. My sweet little angel eager to be trained right. So glad I got to you before anyone could ruin you.”

Another knuckle pushed in and Castiel panted. His breathing hitched and he shoved his face into the pillows with a low whine. He was struggling to maintain his position but when Benny went back to stroking his prostate he shoved back with a moan.

He moved without thought, body instinctively responding to Benny’s touch, as his breathing shuddered.

A hand wrapped around the back of his neck and tightened in warning, “None of that, sugar.” Benny’s voice lowered and his fingers continued against Castiel’s prostate. The weight of Benny’s hand pinning him had Castiel spreading his legs further, knees pressing into the mattress, as Benny continued to press forward. “You can do this. I know your tight little body can take it.”

Castiel wasn’t sure but eventually Benny had loosened him up enough that four fingers were not burning and instead he felt full as they fucked into his ass.  His hole clenched down and he could hear Benny’s breathing. “ _Benny_.” He managed it and his voice didn’t sound normal.

It sounded wrecked, as though he’d gone several rounds without release or similar to the few times Benny had edged him until he’d been a shaking mess. It kind of reminded him of the times Benny had roughly fucked his face and his throat had been scratchy after. “Your hole looks perfect.” Benny’s fingers were moving inside him and Castiel whined low in his throat. “Ready for another?”

He couldn’t form words when a warm hand curled around his cock, giving it several quick strokes, as pleasure raced up his spine and he tightened down around Benny. “Oh.” The word was gasped as his eyes fluttered and his mouth went slack.

“Shhh. I’ve gotcha, angel. I know how empty you get.”

Cool lube squirted into his loose, gaping hole and caused him to jerk as his fingers tightened on the slats. Benny released a sound of appreciation as he dropped the lube back on the bed and moved closer as Castiel panted at the feeling of fingers sinking back into him.

Everything seemed frozen until Benny moved to include his thumb. It brushed teasingly against Castiel’s puffy, stretched rim before Benny began to start working more of his hand inside.

There was some kind of ringing in his ears and everything tunneled down to the burn in his ass, the impossible feeling of full and a hand moving up and down his cock. He struggled to maintain his position as Benny slowly loosened him up and more of his hand started to push inside.

His ass burned, his hole spreading wide to accommodate something the size of Benny’s large hand, as his breathing hitched and his muscles trembled.

Time slowed and his breathing was ragged, skin hot and sensitive, as somehow Benny managed to get his hand inside but the much older man wasn’t done. “My good boy has such a greedy hole. Takin’ my whole hand but I think you can take more. _I know you can_.”

Castiel could feel Benny’s hand inside him, hot and thick, as those thick fingers curled and formed a fist. It stole his breath and when Benny moved it a few times, short little thrusts, Castiel was lost to sensation. He couldn’t think, couldn’t form a single thought, beyond the aching burn and the feeling of too full.

Benny’s hand returned and started to jerk him off, grip just the right amount of pressure, as Castiel’s breathing quickened and his orgasm tightened inside him. He could feel it in his gut and at the base of his spine as Benny dragged it out until he came with a sound that wasn’t human.

He must have blacked out because Castiel’s eyes lazily blinked open and he was laid out on the bed with Benny resting on his legs, idly teasing his hole. “There ya are.” His fingers traced over his sensitive rim and Castiel whimpered at the too much sensation. “Such a pretty hole. Puffy and red. You’re so loose for me, sugar. Don’t worry, you’ll get used to being so full, and now that you’re pliant it’ll be easier.”

Castiel shuddered, “Benny I—” he cleared his throat, “Benny. Please.”

“You are such a good boy for me.” His fingers easily slipped inside and moved to brush against Castiel’s prostate. “Did ya love being fucked full of my fist?”

He could only nod as another whine escaped and his body shuddered. Benny knew exactly how to play his body. He knew how to push Castiel right to the edge, to his limit.

Slowly he was guided back up, on shaky legs and trembling arms, as Benny squirted a liberal amount of lube into his slack hole and followed it up with the pressure of a fist pushing against his rim.

Castiel’s head dipped as he fought to maintain position, sweat making his skin glisten, while he panted and whined as Benny’s fist pushed back into his wrecked hole. It burned just as much as before.

A hand braced on his body while Benny slowly fucked his fist deeper and deeper into Castiel’s tight, oversensitive body. Castiel’s hole spread wide to accomidate the girth of Benny’s fist, his wrist and then some of Benny’s forearm started to sink in.

His mouth fell open on a silent cry as Benny pushed deeper, lazily fucking his arm inside Castiel’s smaller body. In a daze Castiel glanced underneath to actually _see_ Benny’s fist against the thin skin of his belly.

“Oh.” The word popped out of him while Benny fist fucked him, hand braced on Castiel’s ass, as Castiel’s arms threatened to go out from under him.

“So good, sugar, so good for me.” Benny praised as his fist moved, slowly fucking Castiel’s sore ass. “I knew you could do it. I knew my good boy was ready for this.” Castiel’s arms faltered so he ended up with his face mashed against the mattress, ass raised and full of Benny’s arm. “I think you’re ready for three cocks now.”

Castiel blinked, expression slack and breathing ragged. The only thing he could focus on was the feeling of Benny’s fist and arm nestled inside of him.

_Three cocks?_

“You did so well taking two and now my fist…I know a pretty little thing like you is ready to take three.”

Distantly Castiel wondered if the man from before would be one of the two Benny invited into their _secret_ but as Benny’s arm moved he couldn’t focus on anything else. Whines, high and broken sounding, spilled from his lips and his body shuddered as Benny slowly withdrew.

Castiel could feel how his hole gaped, fucked wide open and loose. Behind him Benny whistled lowly in appreciation. “If you could see how ruined your little hole looks, angel. Absolutely beautiful.”

**Author's Note:**

> I don't think I've actually posted fisting on here but I know when I did that kink poll it actually had a bunch of votes for it. As always I hope some of you enjoyed this and that a change of pace was something you welcomed!
> 
> I'm on a Bottom!Cas roll today.


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